TY - JOUR
T1 - Conjugation of resveratrol with RGD and KGD derivatives
AU - Koutsas, C.
AU - Sarigiannis, Y.
AU - Stavropoulos, G.
AU - Liakopoulou-Kyriakides, M.
PY - 2007/10
Y1 - 2007/10
N2 - The reaction between Arg-Gly-Asp (RGD) and Lys-Gly-Asp (KGD) derivatives with 3,4′,5-trihydroxy-transstilbene (resveratrol) was investigated. Knowing that resveratrol, RGD as well as KGD analogues inhibit human platelet aggregation in vitro, it was tempting for us to examine whether their coupling products present enhanced biological activity. Here, we report on the synthesis and identification of these coupling products. The N-protected peptides were synthesized by solid phase technique, using the 2-chlorotrityl-chloride resin, by the method of carbodiimides. Coupling reactions with resveratrol took place in solution using N,N-dicyclohexylcarbodiimide (DCC) as coupling reagent and 4-dimethylaminopyridine (DMAP) as catalyst. The reaction products were purified by reversed phase HPLC and identified by ESI-MS. The mono-esterified resveratrol derivative was the main (or only) reaction product, whereas the di- and the tri-ester (to a less extent) formation was noticed in some cases.
AB - The reaction between Arg-Gly-Asp (RGD) and Lys-Gly-Asp (KGD) derivatives with 3,4′,5-trihydroxy-transstilbene (resveratrol) was investigated. Knowing that resveratrol, RGD as well as KGD analogues inhibit human platelet aggregation in vitro, it was tempting for us to examine whether their coupling products present enhanced biological activity. Here, we report on the synthesis and identification of these coupling products. The N-protected peptides were synthesized by solid phase technique, using the 2-chlorotrityl-chloride resin, by the method of carbodiimides. Coupling reactions with resveratrol took place in solution using N,N-dicyclohexylcarbodiimide (DCC) as coupling reagent and 4-dimethylaminopyridine (DMAP) as catalyst. The reaction products were purified by reversed phase HPLC and identified by ESI-MS. The mono-esterified resveratrol derivative was the main (or only) reaction product, whereas the di- and the tri-ester (to a less extent) formation was noticed in some cases.
KW - Coupling reactions
KW - Esterification
KW - KGD
KW - Resveratrol
KW - RGD
UR - http://www.scopus.com/inward/record.url?scp=36448988298&partnerID=8YFLogxK
U2 - 10.2174/092986607782541141
DO - 10.2174/092986607782541141
M3 - Article
C2 - 18221000
AN - SCOPUS:36448988298
SN - 0929-8665
VL - 14
SP - 1014
EP - 1020
JO - Protein and Peptide Letters
JF - Protein and Peptide Letters
IS - 10
ER -